I figure the upside to the rental scenario is, of course, investing in multiple properties, while a downside would be having to most likely get a conventional loan on the second house with 20+% down and proof of sufficient enough financial reserves to handle two mortgages. 

We have visited the market multiple times in the last six months but remain uncommitted to expanding. 

Despite multiple requests (and promises to do so in text messages) across the span of months, my partner never uploaded the relevant information on this client, including the invoices.

It’s definitely possible to refinance multiple properties under a single loan, often called a portfolio loan, but it depends on the lender.

Test out.

See the stress test above.  

They use PRICE LABS to create these score cards that test your price, data is pulled from Price Labs, well guess what you can access that right from Price Labs you do not need to pay them for that.

Looking to hear what you would do - I've heard of people targeting 1031 Investors to sell large portfolios or multiple buildings but have no idea where I would begin outside of asking a community like Bigger Pockets.

Quote from @Bill Warren: I was hoping to find someone who could help me transfer properties out of my personal name into a series LLC or multiple LLCs.

In the end we decide to go with Digb because the also handle the taxes and multiple LLCs really well.